EP1763302A2 - Composes chimiques - Google Patents

Composes chimiques

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Publication number
EP1763302A2
EP1763302A2 EP05757532A EP05757532A EP1763302A2 EP 1763302 A2 EP1763302 A2 EP 1763302A2 EP 05757532 A EP05757532 A EP 05757532A EP 05757532 A EP05757532 A EP 05757532A EP 1763302 A2 EP1763302 A2 EP 1763302A2
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EP
European Patent Office
Prior art keywords
optionally substituted
alkyl
alkoxy
haloalkyl
heteroaryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP05757532A
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German (de)
English (en)
Other versions
EP1763302B1 (fr
Inventor
Peter Syngenta Crop Protection AG MAIENFISCH
Louis-P. Syngenta Crop Protection AG MOLLEYRES
Jérôme Syngenta Crop Protection AG CASSAYRE
Fredrik Syngenta Crop Protection AG CEDERBAUM
Camilla Syngenta Crop Protection AG CORSI
Thomas Syngenta Crop Protection AG PITTERNA
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Syngenta Participations AG
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Syngenta Participations AG
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Priority to PL05757532T priority Critical patent/PL1763302T3/pl
Publication of EP1763302A2 publication Critical patent/EP1763302A2/fr
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Publication of EP1763302B1 publication Critical patent/EP1763302B1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Definitions

  • the present invention relates to piperidine derivatives, to processes for preparing them, to insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them and to methods of using them to combat and control insect, acarine, mollusc and nematode pests.
  • Piperidine derivatives with fungicidal properties are disclosed in for example in EP494717.
  • the present invention therefore provides a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I):
  • R 1 is hydrogen, optionally substituted alkyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted heterocyclyloxy, cyano, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, formyl, optionally substituted heterocyclyl, optionally substituted alkylthio, NO or NR 13 R 14 where R 13 and R 14 are independently hydrogen, COR 15 , optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroary
  • R 2 is H, hydroxy, optionally substituted alkoxy or optionally substituted alkyl; or R 1 and R 2 together with the groups Y and N form a 5-or 6-membered heterocyclic ring which may optionally contain one further heteroatom selected from O, N or S and which may be optionally substituted by C 1-4 alkyl, C 1-4 haloalkyl or halogen;
  • R 3 is H, OH, halogen or optionally substituted alkyl;
  • R 3a is H or R 3 and R 3a together form a bond;
  • each R 4 is independently halogen, nitro, cyano, optionally substituted C 1-8 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted C 3-7 cycloalky
  • R 8 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl or optionally substituted alkenylcarbonyl; each Ra is independently halogen, hydroxy, cyano, optionally substituted C 1-8 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted C 3-7 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy
  • the compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.
  • Each alkyl moiety either alone or as part of a larger group (such as alkoxy, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl) is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, iso- - A -
  • alkyl groups are suitably C 1 to C 12 alkyl groups, but are preferably C 1 -C 10 , more preferably C 1 -C 8 , even more preferably preferably C 1 -C 6 and most preferably C 1 -C 4 alkyl groups.
  • the optional substituents on an alkyl moiety include one or more of halogen, nitro, cyano, NCS-, C 3-7 cycloalkyl (itself optionally substituted with C 1-6 alkyl or halogen), C 5-7 cycloalkenyl (itself optionally substituted with C 1-6 alkyl or halogen), hydroxy, C 1-10 alkoxy, C 1-10 alkoxy(C 1-10 )alkoxy, tri(C 1-4 )alkylsilyl(C 1-6 )alkoxy, C 1-6 alkoxycarbonyl(C 1-10 )alkoxy, C 1-10 haloalkoxy, aryl(C 1-4 )- alkoxy (where the aryl group is optionally substituted), C 3-7 cycloalkyloxy
  • Alkenyl and alkynyl moieties can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, can be of either the (E)- or ⁇ -configuration. Examples are vinyl, allyl and propargyl.
  • the optional substituents on alkenyl or alkynyl include those optional substituents given above for an alkyl moiety.
  • acyl is optionally substituted C 1-6 alkylcarbonyl (for example acetyl), optionally substituted C 2-6 alkenylcarbonyl, optionally substituted C 2-6 alkynylcarbonyl, optionally substituted arylcarbonyl (for example benzoyl) or optionally substituted heteroarylcarbonyl.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkyl groups are alkyl groups which are substituted with one or more of the same or different halogen atoms and are, for example, CF 3 , CF 2 Cl, CF 3 CH 2 or CHF 2 CH 2 .
  • aryl refers to ring systems which may be mono-, bi- or tricyclic. Examples of such rings include phenyl, naphthalenyl, anthracenyl, indenyl or phenanthrenyl. A preferred aryl group is phenyl.
  • heteroaryl refers to an aromatic ring system containing at least one heteroatom and consisting either of a single ring or of two or more fused rings.
  • single rings will contain up to three and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulphur.
  • groups include furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-tria
  • heteroaromatic radicals include pyridyl, pyrimidyl, triazinyl, thienyl, furyl, oxazolyl, isoxazolyl, 2, 1 ,3 -benzoxadiazole and thiazolyl.
  • heterocycle and heterocyclyl refer to a non-aromatic ring containing up to 10 atoms including one or more (preferably one or two) heteroatoms selected from O, S and N. Examples of such rings include 1,3-dioxolane, tetrahydrofuran and morpholine.
  • heterocyclyl When present, the optional substituents on heterocyclyl include C 1-6 alkyl and C 1-6 haloalkyl as well as those optional substituents given above for an alkyl moiety.
  • Cycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl.
  • Cycloalkenyl includes cyclopentenyl and cyclohexenyl.
  • cycloalkyl or cycloalkenyl include C 1-3 alkyl as well as those optional substituents given above for an alkyl moiety.
  • Carbocyclic rings include aryl, cycloalkyl and cycloalkenyl groups.
  • the optional substituents on aryl or heteroaryl are selected independently, from halogen, nitro, cyano, NCS-, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy- (C 1-6 )alkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl (itself optionally substituted with C 1-6 alkyl or halogen), C 5-7 cycloalkenyl (itself optionally substituted with C 1-6 alkyl or halogen), hydroxy, C 1-10 alkoxy, C 1-10 alkoxy(C 1-1 o)alkoxy, tri(C 1-4 )alkyl- silyl(C 1-6 )alkoxy, C 1-6 alkoxycarbonyl(C 1-10 )alkoxy, C 1-10 haloalkoxy, aryl(C 1-4 )alkoxy (where the aryl group is
  • substituents are independently selected from halogen, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkylthio, C 1-6 haloalkylthio, C 1-6 alkylsulfmyl, C 1-6 haloalkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfonyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, nitro, cyano, CO 2 H, " C 1-6 alkylcarbonyl, C 1-6 alkoxycarbonyl, R 25 R 26 N or R 27 R 28 NC(O); wherein R 25 R 26 N or R 27 R 28 NC(O); wherein R 25 R 26 N or R 27 R 28 NC(O
  • Haloalkenyl groups are alkenyl groups which are substituted with one or more of the same or different halogen atoms. It is to be understood that dialkylamino substituents include those where the dialkyl groups together with the N atom to which they are attached form a five, six or seven- membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which is optionally substituted by one or two independently selected (C 1-6 )alkyl groups. When heterocyclic rings are formed by joining two groups on an N atom, the resulting rings are suitably pyrrolidine, piperidine, thiomorpholine and morpholine each of which maybe substituted by one or two independently selected (C 1-6 ) alkyl groups.
  • the optional substituents on an alkyl moiety include one or more of halogen, nitro, cyano, HO 2 C, C 1-10 alkoxy (itself optionally substituted by C 1-10 alkoxy), aryl(C 1-4 )alkoxy, C 1-10 alkylthio, C 1-10 alkylcarbonyl, C 1-10 alkoxycarbonyl, C 1-6 alkylaminocarbonyl, di(C 1-6 alkyl)aminocarbonyl, (C 1-6 )alkylcarbonyloxy, optionally substituted phenyl, heteroaryl, aryloxy, arylcarbonyloxy, heteroaryloxy, heterocyclyl, heterocyclyloxy, C 3-7 cycloalkyl (itself optionally substituted with (C 1-6 )alkyl or halogen), C 3- 7 cycloalkyloxy, C 5-7 cycloalkenyl, C 1-6 alkylsulfonyl, C 1-6 alkyl
  • the optional substituents on alkenyl or alkynyl include one or more of halogen, aryl and C 3-7 cycloalkyl.
  • a preferred optional substituent for heterocyclyl is C 1-6 alkyl.
  • the optional substituents for cycloalkyl include halogen, cyano and C 1-3 alkyl.
  • the optional substituents for cycloalkenyl include C 1-3 alkyl, halogen and cyano.
  • Preferred groups for T, Y, Ra, R 1 , R 2 , R 3 , R 3a , R 4 and R 8 in any combination thereof are set out below.
  • R 1 is hydrogen, C 1-6 alkyl, C 1-6 cyanoalkyl, C 1-6 haloalkyl, C 3-7 cycloalky ⁇ C ⁇ alkyl, C 1-6 alkoxy(C 1-6 )alkyl, heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group may be optionally substituted by halo, nitro, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 1-6 alkylthio, C 1-6 alkoxycarbonyl, C 1-6 alkylcarbonylamino, arylcarbonyl, or two adjacent positions on the heteroaryl system may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with
  • R 1 is C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy(C 1-6 )alkyl, heteroary ⁇ Ci. 3 )alkyl (wherein the heteroaryl group may be optionally substituted by halo, nitro, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, or two adjacent positions on the heteroaryl system may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen), phenyl(C 1-3 )alkyl (wherein the phenyl group may be optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 ,
  • R 1 is C 1-6 alkyl, C 1-6 haloalkyl, heteroaryl(C 1-3 )alkyl (wherein the heteroaryl group may be optionally substituted by halo, cyano, C 1-6 alkyl, C 1-6 haloalkyl and where the heteroaryl group is a thiazole, pyridine, pyrimidine, pyrazine or pyridazine ring), heteroaryl (optionally substituted by halo, cyano, C 1-6 alkyl, C 1-6 haloalkyl and where the heteroaryl group is a pyridine, pyrimidine, 2,1,3-benzoxadiazole, pyrazine or pyridazine ring), C 1-6 alkoxy, C 1-6 alkoxy(C 1-6 )alkyl, C 1-6 alkylamino, C 1-6 alkyoxy(C 1-6 )alkylamino or heteroaryl(C 1-3 )alkyl (where
  • R 1 is pyridyl (optionally substituted by halo, C 1-3 alkyl or C 1-3 haloalkyl) especially halo-substituted pyridyl. It is preferred that : R R 2 is hydrogen, hydroxy, C 1-6 alkyl or C 1-6 haloalkyl. More preferably R 2 is hydrogen, C 1-4 alkyl or C 1-4 haloalkyl.
  • R 2 is hydrogen or C 1-4 alkyl.
  • R 2 is independently hydrogen or methyl.
  • R 2 is hydrogen. It is preferred that R 3 is hydrogen, hydroxy, halogen, C 1-6 alkyl or C 1-6 haloalkyl.
  • R 3 is hydrogen, hydroxy, halogen,C 1-4 alkyl or C 1-4 haloalkyl.
  • R 3 is hydrogen or C 1-4 alkyl.
  • R 3 is independently hydrogen or methyl.
  • R 3 is hydrogen.
  • R 3a is preferably hydrogen or R 3 and R 3a together form a double bond.
  • each R 4 is independently halogen, cyano, C 1-8 alkyl, C 1-8 haloalkyl, cyanoalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 5-6 cycloalkenyl(C 1-6 )alkyl, C 3-6 alkenyloxy(C 1-6 )alkyl, C 3-6 alkynyloxy(C 1-6 )alkyl, aryloxy(C 1-6 )alkyl, C 1-6 carboxyalkyl, C 1-6 alkylcafbonyl(C 1-6 )alkyl, C 2-6 alkenylcarbonyl(C 1-6 )alkyl, C 2-6 alkynylcarbonyl(C 1-6 )- alkyl, C 1-6 alkoxycarbonyl(C 1-6 )alkyl, C 3-6 alkenyloxycarbonyl(C 1-6 )alkyl
  • heterocyclyl group is optionally substituted by halo, nitro, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy or C 1-6 haloalkoxy
  • C 2-6 alkenyl aminocarbonyl(C 2-6 )alkenyl, C 1-6 alkylaminocarbonyl(C 2-6 )alkenyl, di(C 1-6 )alkylaminocarbonyl(C 2-6 )alkenyl, phenyl(C 2-4 )- alkenyl, (wherein the phenyl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), C 2-6 alkynyl, trimethylsilyl(C 2-6 )alkynyl, aminocarbonyl(C
  • each R 4 is independently halogen, cyano, C 1-8 alkyl, C 1-8 haloalkyl, C 1-8 cyanoalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 2-6 alkynyl, trimethylsilyl(C 2-6 )alkynyl, C 1-6 alkoxycarbonyl, C 3-7 cycloalkyl, C 1-3 alkyl (C 3-7 ) cycloalkyl, phenyl (optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), heterocyclyl (optionally substituted by halo, nitro, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy or C 1-6 haloalkoxy), C 1-8 alk
  • each R 4 is independently halogen, cyano, C 1-8 alkyl, C 1-8 haloalkyl, C 1-8 cyanoalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 2-6 alkynyl, heterocyclyl (optionally substituted by C 1-6 alkyl), C 1-8 alkoxy, C 1-6 haloalkoxy, phenoxy (optionally substituted by halo, cyano, C 1-3 alkyl or C 1-3 haloalkyl), heteroaryloxy (optionally substituted by halo, cyano, C 1-3 alkyl or C 1-3 haloalkyl), di(Ci -8 )alkylamino or 2 adjacent groups R 4 together with the carbon atoms to which they are attached form a 4, 5, 6 or 7 membered carbocylic or heterocyclic ring which may be optionally substituted by halogen; n is 0, 1, 2 or 3.
  • each R 4 is independently fluoro, chloro, bromo, cyano, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl or C 1-3 alkoxy(C 1-3 )alkyl; n is 0, 1, 2 or 3, preferably 0, l or 2. Most preferably each R 4 is independently fluoro, chloro, bromo, C 1-4 alkyl or C 1-4 haloalkyl; n is 1, 2 or 3, preferably 1 or 2.
  • R 8 is C 1-10 alkyl, C 1-10 haloalkyl, aryl(C 1-6 )alkyl (wherein the aryl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), arylcarbonyl-(C 1-6 )alkyl (wherein the aryl group may be optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1- 4 haloalkyl
  • R 8 is phenyl(C 1-4 )alkyl (wherein the phenyl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group is optionally substituted halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), phenyl(C 2-6 )alkenyl (wherein the phenyl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , hal
  • R 51 and R 52 are preferably hydrogen.
  • R 53 and R 54 are preferably hydrogen or halogen, especially hydrogen.
  • R 55 is preferably phenyl substituted with one to three substituents selected from halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino.
  • ring members other than Z and Z' are each independently CH, S, N, NR 4 , O, or CR 4 provided that there are no more than one O or S atoms present in the ring. More preferably the ring
  • benzene is a benzene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, pyrrole, imidazole, quinoline, isoquinoline, thiophene, pyrazole, oxazole, thiazole, isoxazole, isothiazole, [l,2,3]triazole, [l,2,3]oxadiazole or [l,2,3]thiadiazole.
  • ring is a benzene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, pyrrole, imidazole, quinoline, isoquinoline, thiophene, pyrazole, oxazole, thiazole, isoxazole, isothiazole, [l,2,3]triazole, [l,2,3]oxadiazole or [l,2,3]thiadiazole.
  • benzene is a benzene, pyridine, pyrimidine, pyrazine, thiophene or pyrazole ring, especially a benzene ring.
  • Table III provides 1127 compounds of formula Ic wherein the values of R s , R > 4a , T Rj 4b , T RO 4 4 c C and R 4d ⁇ are given in Table 1
  • Table VI provides 1127 compounds of formula If wherein the values of R s , R >4 4 a a , ⁇ Rj4b , r R>4 4 c C and R 4 w d are given in Table 1
  • Table VII provides 1127 compounds of formula Ig
  • Table IX provides 1127 compounds of formula Ii wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1.
  • Table XII provides 1127 compounds of formula Il wherein the values of R ⁇ , R >4a , D R4b , - Rr,4 4 c 0 and R 4 4 d ⁇ are given in Table 1
  • Table XIV provides 1127 compounds of formula hi
  • Table XV provides 1127 compounds of formula Io wherein the values of R > 8 5 , - Rr>4a , r R>4b , ⁇ R>4 4 c C and R 4 4 d ⁇ are given in Table 1
  • Table XVIII provides 1127 compounds of formula Lr wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1.
  • Table XXI provides 1127 compounds of formula Iu wherein the values of R 8 , R >4a , ⁇ R>4b , ⁇ R>4 4 c C and R 4 ⁇ are given in Table 1
  • Table XXVI provides 1127 compounds of formula lab
  • Table XXVII provides 1127 compounds of formula lac wherein the values of R 8 , R , R 4b , T R 5 4 4 c C and R >4 4 d ⁇ are given in Table 1
  • Table XXX provides 1127 compounds of formula Iaf wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XXXII provides 1127 compounds of formula Iah
  • Table XXXIII provides 1127 compounds of formula Iai wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1.
  • Table XXXTV provides 1127 compounds of formula Iaj
  • Table XXXVI provides 1127 compounds of formula IaI wherein the values of R ⁇ R >4a, - Rr>4 4 b b , ⁇ R)4 4 c C and R 4 4 d ⁇ are given in Table 1
  • Table XXXIX provides 1127 compounds of formula Iao wherein the values of R s , R >4a, ⁇ R>4b , T Rj 4 4 C C and R 4d are given in Table 1.
  • Table XL provides 1127 compounds of formula lap
  • Table XLII provides 1127 compounds of formula inquire wherein the values of R 8 , R )4a, ⁇ R > 4 4 b D , ⁇ R)4 4 c C and R 4 4 d ⁇ are given in Table 1.
  • Table XLV provides 1127 compounds of formula Iau wherein the values of R 8 , R ,4a, r R>4 4 b 0 , ⁇ R>4 4 c C and ⁇ C 4d a are given in Table 1
  • Table XLVI provides 1127 compounds of formula lav
  • Table XLVII provides 1127 compounds of formula law
  • Table XLVIII provides 1127 compounds of formula lax
  • Table L provides 1127 compounds of formula Iaab
  • Table LI provides 1127 compounds of formula Iaac wherein the values of R ⁇ R 4 4 a a , ⁇ R->4 4 b b , r R>4 4 o 0 and i ⁇ R>4 4 d ⁇ are given in Table 1
  • Table LII provides 1127 compounds of formula Iaad
  • Table LIV provides 1127 compounds of formula Iaaf wherein the values of R ⁇ R > 4a , R ⁇ 4b , R ⁇ 4 4 c C and R 4 ⁇ are given in Table 1
  • Table LV provides 1127 compounds of formula Iaag
  • Table LVII provides 1127 compounds of formula Iaai wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1.
  • Table LVIII provides 1127 compounds of formula Iaaj
  • Table LIX provides 1127 compounds of formula Iaak
  • Table LX provides 1127 compounds of formula Iaal wherein the values of R 8 , R >4a , ⁇ R>4b , ⁇ R>4*c c and R 4 4 d are given in Table 1.
  • Table LXIII provides 1127 compounds of formula Iaao wherein the values of R , R >4a , ⁇ R>4b , - R D 4 4 C C and R 4 4 d ⁇ are given in Table 1.
  • Table LXV provides 1127 compounds of formula Iaaq
  • Table LXVI provides 1127 compounds of formula Iaar wherein the values of R ⁇ R >4a , r R>4b , ⁇ R)4 4 c Q and R 4 ⁇ are given in Table 1.
  • Table LXIX provides 1127 compounds of formula Iaau wherein the values of R 8 , R >4 w a, D R4b , ⁇ R>4 4 c C and R 4 4 d ⁇ are given in Table 1
  • Table LXXII provides 1127 compounds of formula Iaax
  • Table LXXIII provides 506 compounds of formula Iy
  • Table LXXIV provides 506 compounds of formula Iya
  • Table XCIV provides 506 compounds of formula Iyu
  • Table XCV provides 506 compounds of formula Iyv
  • Pl is R 8 or is a suitable protective group for example a group such as BOC, benzyl or alkyl and S 1 is the group (R 4 )n.
  • a compound of formula 1 maybe obtained from a compound of formula 2 by reaction with a suitable electrophilic species.
  • Compounds of formula 1 where Y is a carbonyl group may be formed by the reaction of compounds of formula 2 with a carboxylic acid derivative of formula R ⁇ C(O)-Z' where Z' is chloride, hydroxy, alkoxy or acyloxy at a temperature between 0°C and 150°C optionally in an organic solvent such as dichloromethane, chloroform or 1 ,2-dichloroethane, optionally in the presence of a tertiary amine base such as triethylamine or diisopropylethylamine and optionally in the presence of a coupling agent such as dicyclohexylcarbodiimide.
  • Compounds of formula 1 where Y is a group of formula S(O) m maybe formed from compounds of formula 2 by treatment with compounds of formula under similar conditions.
  • compounds of formula 1 where Y is a thiocarbonyl group and R 1 is a carbon substituent may be formed by treatment of compounds of formula 1 where Y is a carbonyl group and R 1 is a carbon substituent with a suitable thionating agent such as Lawesson's reagent.
  • a suitable thionating agent such as Lawesson's reagent.
  • sulfur electrophiles of formula R ⁇ S(O) 1n -Cl are either known compounds or may be formed from known compounds by known methods by a person skilled in the art.
  • Compounds of formula 2 may be prepared from compounds of formula 3 by cleavage of the amide bond, according to known methods by a person skilled in the art.
  • Compounds of formula 3 may be obtained from compounds of formula 4 by reaction with an alkylating agent of the formula R 8 -L, where L is chloride, bromide, iodide or a sulfonate (e.g. mesylate or tosylate) or similar leaving group at a temperature of between ambient temperature and 100°C, typically 65 0 C, in an organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane in the presence of a tertiary amine base such as triethylamine or diisopropylethylamine and optionally catalysed by halide salts such as sodium iodide, potassium iodide or tetrabutylammonium iodide.
  • an alkylating agent of the formula R 8 -L where L is chloride, bromide, iodide or a sulfonate (e.g. mesylate or tosylate) or similar
  • a compound of formula 4 may be reacted with an aldehyde of the formula R -CHO at a temperature between ambient temperature and 100°C in an organic solvent such as tetrahydrofuran or ethanol or mixtures of solvents in the presence of a reducing agent such as borane-pyridine complex, sodium borohydride, sodium (triacetoxy)borohydride, sodium cyanoborohydride or such like, to produce a compound of formula 3 where R is CH 2 -R.
  • an organic solvent such as tetrahydrofuran or ethanol or mixtures of solvents
  • a reducing agent such as borane-pyridine complex, sodium borohydride, sodium (triacetoxy)borohydride, sodium cyanoborohydride or such like
  • Compounds of formula 4 may be prepared from compounds of formula 5 where Pl is benzyl or alkyl by a dealkylation reaction, according to known methods by a person skilled in the art. Compounds of formula 4 maybe prepared from compounds of formula 5 where Pl is
  • compounds of formula 4 may be formed by the reaction of compounds of formula 6 where P 1 is BOC by treatment with HCl or H 2 SO 4 in AcOH at a temperature between 0°C and 15O 0 C optionally in an inert organic solvent.
  • Compounds of formula 5 may be prepared from compounds of formula 6 where Pl is benzyl or alkyl by a H 2 O elimination reaction, according to known methods by a person skilled in the art. Most favourable is the treatment of a compound of formula 6 with cone. HCl or H 2 SO 4 in AcOH at a temperature between 0°C and 150°C.
  • compounds of formula 5 maybe prepared from compounds of formula 6 by treatment with SOCl 2 , according to known methods by a person skilled in the art.
  • compounds of formula 5 may be formed by the reaction of compounds of formula 9 with a carboxylic acid derivative of formula t-Bu-C(O)-Z" where Z" is chloride, hydroxy, alkoxy or acyloxy at a temperature between 0°C and 150°C optionally in an inert organic solvent.
  • Compounds of formula 6 maybe prepared from compounds of formula 7 by treatment of lithiated compounds of formula 7 with a piperidinone at a temperature between - 10O 0 C and O 0 C optionally in an inert organic solvent, according to known methods by a person skilled in the art.
  • compounds of formula 1 may be formed by alkylation of compounds of formula 11 as described above for compounds of formula 3.
  • Compounds of formula 11 may be prepared from compounds of formula 10 where P 1 is benzyl or alkyl by a dealkylation reaction, according to known methods by a person skilled in the art.
  • Compounds of formula 10 maybe prepared from compounds of formula 9 by methods described above for the conversion of compounds of formula 2 to compounds of formula 1.
  • Compounds of formula 9 maybe prepared from compounds of formula 6 by a H 2 O elimination reaction, according to known methods by a person skilled in the art. Most favourable is the treatment of a compound of formula 6 with aqueous HCl or H 2 SO 4 in AcOH at a temperature between 0°C and 150°C or with a base in H 2 O and an appropriate solvent.
  • 4-Hydroxy-piperidinyl compounds of the general formula 1 may be prepared according to the reactions of Scheme 2 using synthetic methodologies known by a person skilled in the art and as described above.
  • Pl is R8 or is a suitable protective group for example a group such as BOC, benzyl or alkyl and S 1 is the group (R 4 )n.
  • Piperidinyl compounds of the general formula 1 maybe prepared according to the reactions of Scheme 3 using synthetic methodologies known by a person skilled in the art and as described above.
  • Pl is R8 or is a suitable protective group for example a group such as BOC, benzyl or alkyl and S 1 is the group (R 4 )n.
  • Certain compounds of formula 25 are novel and as such form a further aspect of the invention.
  • piperidinyl-aniline derivatives of the general formula 1 may be prepared according to the reactions of Schemes 8 - 13 where S is the group (R 4 )n using synthetic methodologies known by a person skilled in the art and as described above.
  • a key step in these synthetic routes is a Suzuki coupling reaction to prepare tetrahydro ⁇ yridin-4-yl-aniline derivatives.
  • Other cross coupling reactions such as Stille and Negishi couplings, maybe applied as well.
  • the boronate reagents may be prepared as described in the literature; for example P.R Eastwood, THL 41, 3705 (2000). Examples of coupling reactions are given in Examples 21-23 which describe the synthesis of the compounds in Tables EX23.1 - EX23.11.
  • the compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests.
  • the pests which may be combated and controlled by the use of the, invention compounds include those pests associated with agriculture (which term includes the growing of crops for food and fibre products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies).
  • pest species which may be controlled by the compounds of formula (I) include: Myzus persicae (aphid), Aphis gossypii (aphid), Aphis fabae (aphid), Lygus spp. (capsids), Dysdercus spp. (capsids), Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper), Nezara spp. (stinkbugs), Euschistus spp. (stinkbugs), Leptocorisa spp. (stinkbugs), Frankliniella occidentalis (thrip), Thrips spp.
  • the invention therefore provides a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (T), or a composition containing a compound of formula (I), to a pest, a locus of pest, or to a plant susceptible to attack by a pest,
  • the compounds of formula (I) are preferably used against insects, acarines or nematodes.
  • a compound of formula (I) is usually formulated into a composition which includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surface active agent (SFA).
  • a suitable inert diluent or carrier and, optionally, a surface active agent (SFA).
  • SFA surface active agent
  • SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, • emulsification and wetting).
  • all compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%, of a compound of formula (I).
  • the composition is generally used for the control of pests such that a compound of formula (I) is applied at a rate of from O.lg to 10kg per hectare, preferably from Ig to 6kg per hectare, more preferably from Ig to lkg per hectare.
  • a compound of formula (I) When used in a seed dressing, a compound of formula (I) is used at a rate of O.OOOlg to 1Og (for example 0.00 Ig or 0.05g), preferably 0.005g to 1Og, more preferably 0.005g to 4g, per kilogram of seed.
  • the present invention provides an insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) and a suitable carrier or diluent therefor.
  • the composition is preferably an insecticidal, acaricidal, nematicidal or molluscicidal composition.
  • the invention provides a method of combating and controlling pests at a locus which comprises treating the pests or the locus of the pests with an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a composition comprising a compound of formula (I).
  • the compounds of formula (I) are preferably used against insects, acarines or nematodes.
  • compositions can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations.
  • DP dustable powders
  • SP soluble powders
  • SG water soluble granules
  • WP water dispersible granules
  • GR granules
  • SL soluble concentrates
  • OL oil miscible liquids
  • UL ultra
  • Dustable powders may be prepared by mixing a compound of formula (I) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.
  • solid diluents for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers
  • Soluble powders may be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulphate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).
  • water-soluble inorganic salts such as sodium bicarbonate, sodium carbonate or magnesium sulphate
  • water-soluble organic solids such as a polysaccharide
  • WP Wettable powders
  • WG Water dispersible granules
  • Granules may be formed either by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (I) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, " mineral carbonates, sulphates or phosphates) and drying if necessary.
  • a hard core material such as sands, silicates, " mineral carbonates, sulphates or phosphates
  • Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils).
  • solvents such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters
  • sticking agents such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils.
  • One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).
  • DC Dispersible Concentrates
  • a compound of formula (I) may be prepared by dissolving a compound of formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallisation in a spray tank).
  • Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents).
  • Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as C 8 -C 10 fatty acid dimethylamide) and chlorinated hydrocarbons.
  • aromatic hydrocarbons such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark
  • ketones such as cycl
  • An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment.
  • Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 7O 0 C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion.
  • Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkymaphthalenes) and other appropriate organic solvents which have a low solubility in water.
  • Microemulsions may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation.
  • a compound of formula (I) is present initially in either the water or the solvent/SFA blend.
  • Suitable solvents for use in MEs include those hereinbefore described for use in in ECs or in EWs.
  • An ME may be either an oil-in- water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation.
  • An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.
  • SC Suspension concentrates
  • SCs may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I).
  • SCs may be prepared by ball or bead milling the solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound.
  • One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle.
  • a compound of formula (I) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.
  • Aerosol formulations comprise a compound of formula (I) and a suitable propellant (for example n-butane).
  • a compound of formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurised, hand-actuated spray pumps.
  • a compound of formula (I) may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.
  • Capsule suspensions (CS) may be prepared in a manner similar to the preparation of
  • each oil droplet is encapsulated by a polymeric shell and contains a compound of formula (I) and, optionally, a carrier or diluent therefor.
  • the polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure.
  • the compositions may provide for controlled release of the compound of. formula (I) and they may be used for seed treatment.
  • a compound of formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.
  • a composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of formula (I)).
  • additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of formula (I)).
  • a compound of formula (I) may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS).
  • DS powder for dry seed treatment
  • SS water soluble powder
  • WS water dispersible powder for slurry treatment
  • CS capsule suspension
  • the preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above.
  • Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).
  • Wetting agents, dispersing agents and emulsifying agents maybe surface SFAs of the cationic, anionic, amphoteric or non-ionic type.
  • Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.
  • Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di- zsopropyl- and tri-wopropyl-naphthalene sulphonates), ether sulphates, alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid
  • Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
  • alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof
  • fatty alcohols such as oleyl alcohol or cetyl alcohol
  • alkylphenols such as octylphenol, nonyl
  • Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).
  • hydrophilic colloids such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose
  • swelling clays such as bentonite or attapulgite
  • a compound of formula (I) may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or " roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment.
  • a locus of the pests such as a habitat of the pests, or a growing plant liable to infestation by the pests
  • a compound of formula (I) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
  • Compositions for use as aqueous preparations are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use.
  • These concentrates which may include DCs, SCs, ECs, EWs, MEs SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
  • Such aqueous preparations may contain varying amounts of a compound of formula (I) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
  • a compound of formula (I) may be used in mixtures with fertilisers (for example nitrogen-, potassium- or phosphorus-containing fertilisers).
  • fertilisers for example nitrogen-, potassium- or phosphorus-containing fertilisers.
  • Suitable formulation types include granules of fertiliser.
  • the mixtures suitably contain up to 25% by weight of the compound of formula (I) .
  • the invention therefore also provides a fertiliser composition comprising a fertiliser and a compound of formula (I).
  • compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
  • the compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate.
  • An additional active ingredient may: provide a composition having a broader spectrum of activity or increased persistence at a locus; synergise the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resistance to individual components.
  • the particular additional active ingredient will depend upon the intended utility of the composition.
  • Suitable pesticides include the following: a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, s-bioallethrin, fenfluthrin, prallethrin or 5-benzyl-3-furylmethyl-(E)-(lR,3S)-2,2-dimethyl- 3 -(2-oxothiolan-3 -ylidenemethyl)cyclopropane carboxylate; b) Organophosphates, such as, profenofos, sulprofos,
  • Chloronicotinyl compounds such as imidacloprid, thiacloprid, acetamiprid, nitenpyram or thiamethoxam;
  • Diacylhydrazines such as tebufenozide, chromafenozide or methoxyfenozide;
  • Diphenyl ethers such as diofenolan or pyriproxifen; o) Indoxacarb; p) Chlorfenapyr; or q) Pymetrozine.
  • pesticides having particular targets may be employed in the composition, if appropriate for the intended utility of the composition.
  • selective insecticides for particular crops for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed.
  • insecticides or acaricides specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron).
  • acaricidal ovo-larvicides such as clofentezine, flubenzimine, hexythiazox or tetradifon
  • acaricidal motilicides such as dicofol or propargite
  • acaricides such as bromopropylate or chlorobenzilate
  • growth regulators such
  • fungicidal compounds which may be included in the composition of the invention are (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy- iminoacetamide (SSF-129), 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole- 1 -sulphonamide, ⁇ -[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]- ⁇ -butyrolactone, 4-chloro- 2-cyano-N,N-dimethyl-5-/>-tolylimidazole- 1 -sulfonamide (IKF-916, cyamidazosulfamid), 3 -5-dichloro-N-(3 -chloro- 1 -ethyl- 1 -methyl-2-oxopropyl)-4-methylbenzamide (RH-7281 , zoxamide
  • the compounds of formula (I) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
  • synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.
  • Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.
  • a rice selective herbicide which may be included is propanil.
  • An example of a plant growth regulator for use in cotton is PIXTM.
  • Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW).
  • SE suspoemulsion
  • Step A Preparation of N-(4-Chloro-phenyl)-2,2-dimethyl-propiffnide
  • 4-chloroaniline 25.51 g
  • triethylamine 69.73 ml
  • chloroform 350 ml
  • 2,2-dimethyl-propionyl chloride 25.32 g
  • the resulting solution was stirred at r.t. for 1 hour, then water was added and the mixture extracted three times with ethyl acetate.
  • the combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford 35.8 g of product.
  • M.p. 149-15O 0 C Retention Time HPLC 2.83 min
  • Step B Preparation of N-(4-Chloro-2- ⁇ l-[(E)-3-(4-chloro-phenyl)-allyl]-4-hydroxy- piperidin-4-yl ⁇ -phenyl)-2,2-dimethyl-propionamide
  • This Example illustrates the preparation of 4-Chloro-2- ⁇ l-[(E)-3-(4-chloro-phenyl)-allyl]- 1 ,2,3 ,6-tetrahydro-pyridin-4-yl ⁇ -phenylamine and 4-(2-Amino-5-chloro-phenyl)- 1 -[(E)-3 -(4- chloro-phenyl)-allyl]-piperidin-4-ol.
  • This Example illustrates the preparation of 2-(l-Benzyl-l,2,3,6-tetrahydro-pyridin-4-yl)-4- chloro-phenylamine and 4-(2-Amino-5-chloro-phenyl)-l-benzyl-piperidin-4-ol.
  • Step A Preparation of 4- ⁇ 5-Chloro-2-[(2-chloro-pyridine-4-carbonyl)- amino]phenyl ⁇ -3,6-dihydro ⁇ 2H-pyridine-l-carboxylic acid 1-chloro-ethyl ester
  • Step A Preparation of N-(4-Fluoro-phenyl)-2,2-dimethyl-propionamide
  • 4-fluoroaniline 50.0 g
  • triethylamine 157 ml
  • 2,2-dimethyl-propionyl chloride 58.0 ml
  • the resulting solution was stirred at r.t. for 2 hour, then water was added and the mixture extracted three times with ethyl acetate.
  • the combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford 86.0 g of the title compound.
  • M.p. 124-125 0 C Retention Time HPLC 2.57 min
  • Step B Preparation of N-(4-Fluoro-2- ⁇ l-[(E)-3-(4-chloro-phenyl)-allyl]-4-hydroxy- piperidin-4-yl ⁇ -phenyl)-2,2-dimethyl-propionamide
  • N-(4-Fluoro-2-piperidin-4-yl-phenyl)-2,2-dimethyl-propionamide (380 mg) was dissolved in CHCl 3 (20 ml) and treated with triethyl amine (0.260 mg). Then, a solution of l-((E)-3- chloro-propenyl)-4-chloro-benzene (255 mg) was added. After stirring for 16 hours at r.t. the mixture was filtrated and concentrated in vacuo. The residue was subjected to silica gel chromatography (hexane:ethyl acetate:triethyl amine 74:24:2) to afford the title product (380 mg). M.p. 174-176 0 C; Retention Time HPLC 2.37 min; MS (ES+) 4.29 (M+H + ).
  • Triethylamine (2.8 ml) was added to a stirred solution of the compound obtained in example 18 (2.66 g) in dichloromethane (100 ml); the solution was cooled to 0°C and 2- chloroisonicotinoyl chloride (prepared from 2.05 g of 2-chloroisonicotinic acid and 1.46 ml of oxalyl chloride in 50 ml dichloromethane) was added. The resulting mixture was stirred at room temperature for 12 hours, poured into water, extracted two times with dichloromethane; the combined organic layers were dried over sodium sulfate and concentrated in vacuo.
  • 2- chloroisonicotinoyl chloride prepared from 2.05 g of 2-chloroisonicotinic acid and 1.46 ml of oxalyl chloride in 50 ml dichloromethane
  • Step A l-(t-Butoxycarbonyl)-4-tributylstannyl-l,2,3,6-tetrahydropyridine (2.12 g, prepared in 2 steps from l-(t-butoxycarbonyl)-piperidin-4-one according to WO 0123381) was dissolved in toluene (45 ml) in a dried, nitrogen-flushed flask. 2-Chloro-3-nitropyridine (712 mg) and palladium tetrakis(triphenylphosphine) (130 mg) were added and the solution was heated at 110°C for 16 hours.
  • Step B Hydrazine monohydrate (0.4 ml) was added to a suspension of Raney nickel (50% slurry in water, 200 mg) and the product obtained in Step A (240 mg) in ethanol (10 ml). After 4 hours stirring, the reaction mixture was filtered over Hyfio and the solvent removed in vacuo. The residue was dissolved in ethyl acetate, dried over sodium sulfate, filtered and concentrated in vacuo to afford 3-amino-3',6'-dihydro-2'H-[2,4']bipyridinyl-r-carboxylic acid tert-butyl ester (200 mg) as white cystals. M.p.
  • Step C The product obtained in Step B (815 mg) was reduced by transfer hydrogenation using 10% Pd/C (200 mg) and ammonium formate (935 mg) in ethanol (40 ml) at 60°C for 45 min.
  • Step D sodium bicarbonate (714 mg) was added to a stirred solution of the compound obtained in Step C (785 mg) in dichloromethane (30 ml); the solution was then treated with 2-chloro-isonicotinoyl chloride (500 mg) and the resulting mixture was stirred at room temperature for 1 hour, poured into water, extracted two times with dichloromethane, the combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford 3-[(2-Chloro-pyridine-4-carbonyl)-amino]-3',4',5 t ,6'-tetrahydro-2 ⁇ -[2,4']bipyridinyl-r- carboxylic acid tert-butyl ester (1.2 g).
  • Step E A solution of the compound obtained in Step D (834 mg) in dichloromethane (40 ml) was treated with trifiuoroacetic acid (4 ml) for 5 hours at room temperature. The reaction mixture was concentrated in vacuo and then dried under high vacuum for 1 hour. The residue was dissolved in acetonitrile (40 ml), diisopropylethylamine (1.8 ml) and 4- chlorocinnamyl chloride (380 mg) were added. The solution was stirred 20 hours at room temperature, the solvent was removed in vacuo and the residue was subjected to silica gel chromatography (ethyl acetate:methanol 95:5) to afford the title product (409 mg) as a yellow solid. M.p.
  • This Example illustrates the preparation of 2-Chloro-N- ⁇ 5-chloro-l'-[(E)-3-(4-chloro- ⁇ henyl)-allyl]-r,2 l ,3 l ,4',5',6 l -hexahydro-[2,4']bi ⁇ yridinyl-3-yl ⁇ -isonicotinamide.
  • Cotton leaf discs were placed on agar in a 24- well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with 5 L 1 larvae. The samples were checked for mortality, repellent effect, feeding behaviour, and growth regulation 3 days after treatment (DAT). The following compounds gave at least 80% control of Spodoptera littoralis: Iaaa-3 and Iaaa-49. Heliothis virescens ( Tobacco budworm):
  • Aedes aegypti Yellow fever mosquito
  • Aedes larvae (L2) together with a nutrition mixture are placed in 96-well microtiter plates. Test solutions at an application rate of 2ppm are pipetted into the wells. 2 days later, insects were checked for mortality and growth inhibition. The following compounds gave at least 80% control of Aedes aegypti: Ia-53, Iaaa-3, Iaaa-26, Iaaa-49, Iaaa-52, Iaab-26, Iaac-26 and Iaai-26.

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  • Life Sciences & Earth Sciences (AREA)
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  • Wood Science & Technology (AREA)
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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
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  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

La présente invention concerne l'utilisation d'un composé de formule (I), dans laquelle Y représente une liaison unique, C=O, C=S ou S(O)m où m est égal à 0, 1, ou 2, l'anneau constitue un anneau aromatique à 6 éléments ou un anneau hétéroaromatique à 5 ou 6 éléments, Z et Z' désignent =C- ou -N-, à condition qu'ils soient tous deux différents de N, R1, R2 R3, R3a, R4, R8 et Ra représentent des groupes organiques spécifiques et n et p sont indépendamment égaux à 0, 1, 2, 3 ou 4 ou l'utilisation de sels ou de N-oxydes associés ou l'utilisation de compositions les contenant, dans la lutte contre les insectes, les acariens, les nématodes ou les mollusques. Cette invention a aussi pour objet de nouveaux composés.
EP05757532A 2004-06-28 2005-06-22 Composes chimiques Active EP1763302B1 (fr)

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US20090042938A1 (en) 2009-02-12
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